A Darkened Destiny
by AprilC3604
Summary: Castiel never pulled Dean from hell. He stayed there losing himself everyday and soon became the new Alistair. Sam was left alone, following Rudy toward his dark destiney. The angels have to come up with a plan to save the world.DARK!MATURE!OOC!DeanOC
1. Chapter 1

**Summary: **Castiel never showed up that day to pull Dean from hell. Dean was left there, losing a little peace of him everyday. Sam was left alone, following Ruby toward is true destiny, killing a few head demons along the way, Alistair being one. This is a DARK what if story. Not real romance, Dean and Sam are OOC. You are warned. This contains dark themes, sexual content, and other.

**Warning! Dark Dean, Sexual Content.**** Don't like then move along : ) Thanks.**

****Prologue****

_It was once said that the__ longer you are in hell the more your humanity slips away. That is what happened to Dean Winchester. After he said yes to Alistair he started ripping people apart to try and get rid of his own pain. Soon that pain was gone. He felt nothing any more. No pain, no sorrow, no feeling what so ever and that worst part of it was…he liked it. He liked it a lot. He liked the power. There was a new torture master in hell and his name was Dean…THE Dean._

_My name is Jennifer Jackson and I have been here in hell for fifty years now, twenty years less that Dean who was on his seventieth. I came here after I made a deal to have my parent killed. Believe me when I say it's not what you think. They weren't perfect and did some bad things to me. Sure that's not a reason to kill them but I was young. I was only fourteen years old. Ten years after the hell hounds killed me and dragged me here. That is when Dean first saw me. When those evil eyes connected with mine I knew it was over. I was his forever and there was nothing I could do. But just like Dean I lost all feeling after so long. I was his slave and you know what…..I kind of liked it. _

I knelt there on the cold floor waiting in the mess of my own arousal. I knew what was coming. The hot wetness all over my legs still flowed slowly from between my thighs. I whimpered pitifully, waiting for the next assault to my battered body. Out of the darkness he touched me, tugging hard at my nipples that were bruised and sore. Only one person had a touch like his. I yelped and the heat of his palm across me face sent stars before my eyes and fireworks exploded across my pussy. _**Punish me**_I thought. Every atom of my being buzzed with want for the pain he could inflict upon me. What was wrong with me? This was not normal. I was changing inside and out. I felt it everyday.

"You are not to speak, to moan, to groan or scream." he growled at me, his voice almost a whisper it was so low. I tried so hard to obey him, God I tried hard to be the good little slave to be used as he sought fit. Some days were harder than others. His request were sometimes difficult for me but I tried.

I nodded quickly as he pressed his hard cock roughly against my mouth, I opened for him willingly. My lips curled back like the petals of a flower on a spring day. The head of him prodded the back of my throat thrust after thrust and I tried to swallow him, desperately tried to fit all of him down my throat but he was so large.

His hands, those big strong hands clutched at my hair tight, fingers intertwined there in ever curly lock as he pulled my face to meet his thrusts. "Take it baby." He said. It was a order and I tried not to moan as rivers of my excitement poured from me. Sucking him had become a turn on to me. I don't why but it was. The taste of him was like a drug to me. Pain always made me so excited but we all like it a little rough from time to time. This pain was better than the pain others were feeling, the pain of losing someone or just being ripped apart. I would take sexual pain any day.

I could here him breathing steady and even but my breath was coming in short quick gasps, not from lack of air because deep throating. The sheer power of him I could almost feel him deep in my pussy. **'Take me please!'** my mind screamed over and over again. My clit throbbed and my pussy pulsed I couldn't help. I had to touch myself. As soon as my finger tips brushed across me clit my orgasm slowly ripping through me, a scream was forming in my chest and rising up to my throat and on one of his thrusts as deep moan erupted from me as wave after wave of orgasm pushed through me. My extreme pleasure squirted down my thighs and my juices washed across my knees on the hard cold concrete floor. I knew Dean had heard me and he knew what I had done. It was a rule. I was never to cum unless he touched me and told me too but I couldn't help it. The thing he made me feel were sinful….almost evil.

"Jennie, Jennie, Jennie. You Bitch!" He said pulling himself from my mouth, depriving me of the taste of him.

I groaned and leaned toward him desperately trying to wedge him back in my mouth but the only thing that filled my mouth then was the metallic taste of my blood as he slapped me so hard that I fell backwards onto the floor. Another moan escaped me as I lay there quivering. A light came on above me and I could see in his hand the belt that often left such delicious welts across my body in places that another man would never see. He wanted them to see it. It was his mark and his only, warning other to stay away from me or else.

"Get up!" His commands were like words from the Gods or I should say the Devil. I knew I had to do what he asked and do it fast. I stood up and was face to face with Dean, the gorgeous evil man. "Turn around and lean on the bed" he smiled at me.

I did what I was told and my breathing quickened with fear….excitement.

"Why must you constantly disobey me?" He asked just before I felt the belt strike me hard. "Maybe because you like it rough." He said and hit me again. It was the truth. Maybe I liked keeping him happy and fear is what he loved. He loved control. As long as I was the only one we could both be happy.

"Do you like it?" he asked. I could see the grin across his lips without having to see him. I knew him so well, my perfect, handsome, sexy Master. "Well?" he expected and answer this time from me.

"Yes." I whispered as a small shudder moved through me. "Oh yes."

My legs felt so weak and I almost could not stand. My mind reeled and I could see him in my head. My pussy throbbed again and I felt myself losing control and then the blows stopped. His lips were dangerously close to my ears his breathing was heavy and ragged, his voice was the deep growl. "Spread your legs." He growled calmly.

I did and I felt him press against me, his chest to my back, his cock teasing my wet center. I was his property, his slave to use as he saw fit. He caressed his way to my collar bone and closed his hand on my throat squeezing. "So beautiful….so mine." He said as he thrust hard into me. I screamed out loud that I was sure people on earth could hear me. He pounded and pounded away at me. "Say it." He growled.

I knew what he wanted and I was happy to give it to him, "Yours! I'm yours! Take me!"

"Yes." He said as he pulled he against him, never slowing down, "I know you like it."

"Yes…Dean!"

"Say it again." He said and gave my ass a hard slap.

"Dean!" I screamed.

"I want you to cum now, harder than before. Soak me." He commanded.

As always I did what I was told. My body convulsed and cum flowed from me down my legs and pooled at my feet. I felt him cum inside me and it made my orgasm stronger. He loosened his grip on my neck and I moaned over and over again, each time it became louder and louder.

Once we were done I collapsed, shuddering as the strength of my orgasms weakened. He let me go and I slumped to the floor in the cold wetness of my own excitement. He stepped away from me and got dressed. I could hear his foot steps fading toward the door. I whimpered as he unlocked the door. Just as he was closing it he said, "This room better be clean by the time I come back down here."

"Yes, Dean. Anything you want." I whispered trying to bring myself to my knees. Who knew when he'd come back down here. There was nothing or no one down here but me. I was his own personal slave, punished for his pleasure, a human rag to clean the mess off of his cold concrete floor. This was my hell…. or was it my heaven? I was lost. I could feel everything good inside me slowly slipping away. Maybe that's what he wanted. I was never really sure. I was here to serve him. There was no changing that. At least not now and even if I could I can't say I would. I was fucked up inside. But that's the point of hell isn't it? To take everything away from you?

I thought of many things as I sat here alone, wrapped up in nothing but a dirty sheet. My cave, my room. No one knew where Dean slept or even if he did. Where ever it was it had to be better than this. One day maybe I will be taking up to the main part. Then I would be with him. As for now I was a pet, a toy and that was it. I can live with that for now. As long as I got more of him. I wasn't afraid of him. I was afraid of being alone.

Sometimes I would wonder when I looked into his eyes and saw a hint of a human and it made me wonder, who was he and how did he get here? What did he do that was so bad? I had many questions. Maybe one day I would have answers. One day things were going to be different, I could feel it. I just wished I knew how right I was.

***So this will be the only chapter with Jennifer's POV unless you like it like that. This was an intro. Coming up will be more or Jennifer and Dean and the master salve relationship. Sam will come into the picture and you will find out what is going on up on earth. So stay tuned for that. Ok Review time. This was sooo different for me and like I said don't look for candle light dinners and lots of romance in this one. At least not the good kind. SO PLEASE REVIEW AND YOU WILL HAVE MORE : )**


	2. Chapter 2

**Chapter One**

**A Year Later**

Jennifer sat on her old mattress with the sheet wrapped around her bruised body. It had been two day since she last saw Dean. She had only a few hours of sleep. The screams and cried for help would keep her awake at night. This was the worst part of hell to her….being alone. She could everything around her. She hated it. Most would think she was crazy but she wanted Dean.

She sat there with her back to the cold wall and her knees pulled to her chest. She heard foot steps and her face brightened up a little. He was coming for her finally. At least she would have some contact. The door flew open and there he was. Arms crossed, smile on his face, knife in his hand. "Morning my pet." He said.

"Morning s-sir." She said and tucked her dirty hair behind her ears. "What can I do for you?" She asked him.

"Get up and get over her." He told her.

She did what he asked and walked over to him, holding the sheet to her chest. Dean looked her over. Her eye was black, her lip busted and he smiled as he ran his thumb across her bottom lip again, "Are you going to disobey me again?" he asked and Jennie shook her head, "I want to hear you say it!" he yelled.

"N-No s-sir."

"Good. You swear to give into my every need, every want, desire?"

"Y-yes."

Dean smiled. That was just what he needed to hear, "Time to come with me." He said and grabbed her by the back of the neck and pulled her out of the room.

Jennifer was scared for the first time in a long time. Where was he taking her? What was he going to do to her? Either way there was nothing she could do about it. She had to go and take what he gave her. At least she was out of the room.

Dean pulled her down the dark hallways and the screams were getting closer. She knew where she was going and now she was scared. Not of him but of what was going to happen to her. She couldn't be put back on the rack. She stopped and turned to him. "Please Dean. Please don't take me back there. I-I'll do anything. I can do better for you. Please." She cried.

Dean smiled. He loved the fear in her. He loved the power over her. He proved that she was his and it was time for everyone to know that. He just gave her another look before grabbing her roughly again and pulling her toward the room. Tears fell from her eyes. He was putting her back and she knew it. He was done with her. She let him down now she was going to suffer.

The doors opened and they walked in. The smell of sulfur and blood filled the air, screams echoing. "Please." she whispered.

Dean turned to her and pushed her against the wall, "Stand here. Don't you think about moving." He warned her before turning and walking over to a few demons that were getting ready to rip apart another soul.

Jennie closed her eyes as she watched them go to work. She hated this. She wanted to go back in her room. She never thought it would be like this.

"What's wrong baby? Don't like what you see? Jennie looked to her left and saw a very large man with black eyes standing next to her. He smiled as he reached out his hand and ran his fingers over her bare shoulder. "Don't worry. I'm going to make you scream." He said as he looked her up and down.

Jennie felt a chill run up her spine. This was it. Dean was giving her to another. She was losing him. She knew this is when hell was really going to start. That was until she heard Dean.

"Hey! Get the fuck away from her!" he yelled.

Jennie opened her eyes and saw Dean walking over to them and she sighed. Thank….whoever.

"What's wrong Dean? Never learned to share your toys?" The demon laughed.

Dean curled up his lip as he moved in closer and pulled out a large blade. Without even blinking he stuck it deep within the demons chest and watched as he fell to the ground. Jennie stood there still gripping the sheet tight. She was shocked but relieved. Dean wasn't giving her up.

Dean wiped the blade off and glared over at Jennie, "What did you say to him?"

"N-Nothing. He touched me." She said. "I would never speak to him. I swear."

"You better not have."

Dean pulled her from the wall and walked her into the middle of the room, "Listen up! No one is to look, talk, or think about touching her! She is mine to do with as I please. Do you understand me!" he yelled.

"Yes sir." They said.

"Good. Now get back to work." Dean said.

Dean grabbed her by the wrist and pulled her down the hallways to their left. Jennie had never been down there before. Where was he taking her? What lies ahead? This behavior was new. She was something different in Dean. Still the same evil as always but there was a hint of something else. He wanted more from her and she knew it.

They walked down to a set of double doors and Dean pushed them open. It led to yet another hallway. He held onto her tight as the walked a few step and came to another door on their right. Dean stopped and pulled out a key and unlocked the door. When he pushed it open he turned on the lights and Jennie looked around. This must be his bedroom. It was a lot nicer than the room but then again he was torture master so it must have its perks.

"Get in." Dean told her.

Jennie walked into the room and looked around. There was a large bed in the middle of the room and a bathroom to the side. It was almost like a cheap motel room but for hell it was like a room at the Hilton.

"Is-is this yours?" she asked.

"This is mine." Dean smiled, "And now yours as long as you do everything I say when I say it. I want you up here serving me, doing what I ask of you. If I say jump you say how high. No matter what I ask you better do it or I may just hand you over to a few friends of mine. Do I make myself clear?"

"Yes sir. I'll do anything for you. Just…please….." she stopped herself. She was the last person to ask anything of him.

"Please what Jennie?" Dean asked her in a low tone.

"Don't… don't let them hurt me. Please."

A smirked came to Dean's face, "Do they scare you?" he asked and she nodded, "Do I scare you Jennie?"

"A little."

"But you like it don't you?"

"Yes." She answered in a whisper. He scared her but that was a different kind of fear, the kind that she craved, the kind that made her long for him to take her in ways she would never ask or beg another to do.

"You'll do anything for me?" He asked and pulled her against him. Jennie looked up and him and nodded, "Then prove it...right now. Let it be known to everyone that you belong to me."

Jennie bit on her bottom lip as she unwrapped the sheet and let it drop to the floor. Her heart was racing. Why... she didn't know. They have done this hundreds of time but this time was different. He wanted them both to be heard. She had to give everything she had to this man right here and right now. she had to figure out what made a man like this scream. Easier said than done.

Jennie stood up on her tippy toes and pressed her lips to his. Their tongues tangled. She only broke away from his kisses long enough to change position and gasp for much needed air. His hands wrapped around her, pulling her closer.

Fueling her desire, he pulled her leg up around his hip, pressing his groin against her. Using the grip he had on her hips, he turned them, smashing her into the wall as his body crushed hers with bruising force.

Jennie reached down and got the button to his slacks open, jerking down his zipper and pushed them down to the floor. She had never been this grabby with him, in fact she was never to touch him unless asked….but then again he wanted this.

Kissing him hard, her free hand came up cupping the back of his neck, teasing his lips with the tip of her tongue and nipping at them. She stayed firmly pressed back against the wall and pressing herself against his crotch slowly creating a much needed and desired friction. There was no real thought going on in her head she just giving him what he wanted.

Dean hand fisted in her hair as he pushed her harder against the wall, grinding his rock hard cock up against her, hoping it would torment her further. He was not being gentle, not in his kisses, or in his touches, but he wasn't hurting her like before. She grunted hard, whimpering hard as she bit at his lips trying to get him to kiss her. Tilting her head back moaning as she felt his hard still covered cock press against her warm center. "Tell me you want it!" Dean demanded.

"I-I want it."

"I cant hear you." he said and pulled on her hair harder making her yelp.

"I want it!" she screamed.

Dean smirked, "Show me."

Running her nails down his stomach under his shirt, she rolled her hips up against his only to get slammed back into the wall. Turning her head she growled slightly against his ear, "I want you... now" she said again, licking and tugging on his earlobe and kept trying to pull him closer as she wrapped her leg tighter around his waist. Dean groaned a little and she took that as a good sign.

Dean wasn't sure if she knew just how sexy it was for her to be aggressive and submissive all in the same gesture. It was hot, plain and simple. He gripped her leg, rubbing her skin roughly, almost bruisingly hard. He was going to fuck her within an inch of her life.

Her arms moved above her head thrusting her hips against his. Jennie could feel him growing harder as he continued to grind back against her. Sliding her hands along his chest, she was so tempted to rip his shirt open and just push him down on the floor and fuck him but the fact that he was being so much more aggressive and taking his anger out this way, she was almost daring him to keep going. Her hands slid down over his ass. With one hand she pushed his boxers down, his throbbing hard cock springing from its cotton prison. Without warning Dean thrust two fingers into her, hoping like hell she was as wet as she needed to be. Jennie thumped her head back and pushed his shirt up and ran her hands along his stomach and around his back jerking him closer while taking in a soft quick breath when his digits found her tight center, hot and wet for him.

Clenching her jaw she pushed his hand back and stroked the base of his cock whispering next to his ear. "Take me Dean…please just fuck me." She had a low, husky and demanding tone. "God just fuck me!" she smacked his ass gripping it tightly. She was really crossing the line now and may pay for this later but by the look on his face….so far so good.

An evil, almost sadistic chuckle rumbled through his chest as he bit at her neck hard and marked her. like many times before, "You know I should leave you here wet and begging for me." He said as he licked the broken skin, "But I want you and I'm not going to deny myself your sweet, hot pussy," he rasped as he pushed her hand away and rammed his cock inside her with an almost bruising force.

"Oh fuck!" she screamed as loud as she could. That is what he wanted after all. He wanted the other to hear hm claiming her.

Falling back against the wall Jennie gripped his firm biceps and thrusted back up against him hard, whimpering soft just giving it back to him as hard as he was giving it. He groaned so low in his chest it felt like it had come from his toes, as he fucked her. She was so hot, her slick heat fueled by her desire for him. He knew what he did to her. He broke her, made her crave him and he loved it and it just made him fuck her harder. He tugged on her hair as she gripped his shirt tightly, her knuckles turning white as she pulled him closer and attaching his lips.

Whimpering hard she found his tongue, dueling for control of the kiss. Cupping the back of his neck she pulled her lips from his, attack his neck with her lips and teeth, leaving marks that were probably unable to hide but she could careless, he just felt so fucking good. "Oh fuck Jennie." He yelled as she bit down hard. "Bitch!" but he liked it. He liked her taking something back from him.

Unable to speak only moan he just fucked her, getting out his anger, his frustration, his need out as he did so. Even when he was furious at her he wanted her and could not keep his hands off her or his cock out of her it seemed. It was all worth it to be inside her like this, pounding her, taking her, owning her.

Falling back against the wall, Jennie's long leg wrapped around his waist, pulling him closer. "Dean….Oh Dean take me harder!" she screamed again. She knew it was like fuel for him. "Need…want to cum."

"You want me to make you cum?" Dean asked as he pounded into her harder and more forceful, "Beg me." He growled.

"Please…Please make me cum!" Dean could see she was almost in tear. He knew what she wanted.

"Not yet." He smiled.

Her slick and warm walls forcefully tightened around his pulsating shaft. With his thrusts almost forcing her up off both feet she groaned. Their moans and growls mixed with the sounds of their skin smacking against each other's. Feeling her orgasm growing closer she tried to keep it at bay wanting him to cum just has hard with her.

He was getting there, the closer she got the closer he got; that familiar feeling of needed to explode in her starting to creep up from his toes, making the thrusts harder and faster, trying so hard to keep the control a little bit longer.

Her walls clenching him tighter and finally he spoke. "Cum for me...cum hard. Let them hear what I do to you." he ordered, his voice still commanding but raw with need.

His body pressing tightly against hers was all she needed to send her over. "Dean! Fuck! Oh yes Dean!" She was instantly filled with euphoria as she came. Her walls so tight they threatened to push his cock from her throbbing heat but she pulled him closer so he could ride out his orgasm.

Dean pushed back in harder and deeper until her orgasm hit with such a force that it pulled his out of him, making him cum hard, "Jennie, shit!"

His vision went white as his eyes rolled back into his head, and his last attempts at thrusts were erratic but forceful. In that moment, he was so vulnerable, in her hands he was helpless as the feeling of exaltation swept over him, making him forget anything and everything except how she made him feel and the sheer ecstasy at coming inside her.

She was weak against the wall, thumping her head back letting out a soft sigh even though she was out of breath. Licking her lips she raked her fingers through his hair then leaned in kissing his lips. Panting hot against his lips she closed her eyes just loving that moment right after orgasm, that moment when everything just feels so perfect and right….even for hell.

Dropping her leg from around his waist then a small whimper escaped from her lips. Feeling him slip from her wet and warm center, she pulled him close again just to keep kissing him. "Did I please you?"

"Dean smiled as he brushed her bottom lips with his thumb, "Yes...for now."

"What should I do for you now my master?"

"You have two minutes to go clean yourself up. I felt you something inside to wear. Do not leave this room. Are we clear?

"Yes sir."

"Good."

Dean pulled his boxers and jeans back up and fastened them before walking out of the room and locking it.

Jennie stood there for a second still trying to get herself together. she had a feeling this was the start of something new. Good or bad she didn't know yet but something was different.

**X~X~X~X~X~X~X~X~X~X~X~X~X~X~X~X~X~X~X**

Sam sat there in yet another dumpy motel room with a bottle of whiskey in his hands as he flipped through the channels. Dean had been gone 8 months now and there was no getting him back. He knew that now. Now all he wanted to do was get revenge on Lilith and he was going to do whatever it took. Sure he gave Dean is word but if roles were reversed Dean would do the same thing and he knew it.

The door flew open and Sam turned to see Ruby walking in the room. "Where the hell have you been?" Sam asked.

"Out. Trying to find Lilith and picking you up a little something. Its in the trunk or I guess I should say he." she smiled.

"About damn time. Who is it?"

"I don't know. Just so lower level demons possessing some poor bastard. Do you really care?" she asked.

"Not really." Sam said. "Let's just get this over with and find Lilith." Sam said.

Over the passed few months he had really changes. He felt nothing for no one. He was consumed with hunting down Lilith. That is all that mattered to him now. Dean was gone. He had nothing else keeping him straight. Maybe that was for the best.

***Thanks for the alerts and reviews. You guys are awesome! So there was a little clip of Sam for you. More to come so don't worry and also Cas will come into play next chapter. We are just getting warmed up ; ) Ok so you know the drill, if you want more PLEASE review!**


	3. Chapter 3

**Chapter Two**

Jennie woke up the next morning and rolled over to see a note by her head: _Get up and get dress in the clothing I laid out. If you are still asleep when I get back you will be punished...__Dean_

Jennie wasn't sure how much longer she had until Dean got back so she jumped out of bed and quickie put on the black corset he had laid out for her. It was small on her but then again maybe that was the point. He would be able to see all of her whenever he wanted.

Just as she got it on the bedroom door flew open and Jennie jumped. She turned around and saw Dean standing there with blood on his hands like always. Dean stood there and looked her over, "A few more minute earlier and you would be in trouble." He said and closed the door.

"I-I'm sorry I wasn't up before you. It won't happen again I swear." She said fearing what he must be thinking right now.

"I know." He said and walked over to her, "But I've had a really busy morning and I need you right now tp please me." He said and threw her on the bed. He flashed her a wicked grin and said, "You are going to stay here until I am satisfied. You are mine and I will do with you whatever I please."

Shivers ran down her spine as he sat her up. She could feel his breath against her neck as he reached around her and started to untie the corset. Jennie grabbed this opportunity to try and kiss him but he just moved away and got behind her on the bed. He wrapped his legs around her and pulled her back. She felt the corset begin to slip down and her brushed his hand over her shoulder. His hands brush the skin of her back, moving under the corset, making it fall off as he reached for her breasts. Jennie moaned quietly and arched her back as he grabbed hold of them squeezed.

Gently he then moved his fingertips up to her nipples, circling them playfully before pinching and twisting them, making her gasp, "Dean..."

Jennie smiled and turned round, pushing him backwards and trying to hold him down with her legs but he grabbed her wrists and pins them to her sides. She sighed then he says, "I don't think so. You belong to me. Not the other way around."

Dean sat up and pushed her backwards. Her thighs were pressed against his hips as he moves one hand from behind her back to her shoulder and traced his other hand between her breasts, down over her stomach and over one hip to her knee. "So sexy baby."

He moved his hand back up the inside of her thigh and over the to lace thong he set out for her. Dean again takes her wrists and pins them above her head with one of his strong hands. She felt his other hand teasing her, running over her hips and thighs but not where she wanted it. She knew she couldn't take it much longer and so she pleaded, "Please, stop this teasing. Please just fuck me. Claim me again."

She heard him laughing then switch to a more serious tone. "How many times do I have to remind you? You are mine and I will do to you whatever I want!" He growls in her ear then nibbles on it as he ties both arms to the bed. "You need to learn to stop being so impatient." Dean moved off the bed and Jennie closed her eyes. She could hear his shirt drop to the floor then his zipper.

After he had undressed himself he climbed on top of her and pressed his hard cock to her lips. "Suck it," he said, pressing it harder into her mouth. Jennie started to explore it with her tongue, licking the very tip gently before taking it into her mouth, sucking it as she ran her tongue on the soft underneath of his shaft. She began to suck harder as she heard him moan, taking as much of him into her mouth as she could. "Fuck... baby. Just like that." Dean moaned and ran his fingers through her hair.

She felt his cock getting even harder in her mouth and he started to pull away. Jennie then ran her teeth along his shaft and bite it gently, not about to let him get away. "Being greedy aren't we?" He said and removed himself completely. "You will suck it again later. Remember we do have the rest of our lives." Jennie watched him grin as he moved to the end of the bed.

His lips kissed up her legs nibbling as he passed her thighs then stopping to kiss just below her belly button. She felt his fingertips running along the top of the thong, tickling the delicate skin below, causing her to arch her back. He then slowly slid the thong down, kissing her hips and around her pussy. The next thing she felt was two of his fingers plunging into me. "Uh Dean!"

"Nice and wet I see," he said before removing them and then putting them in her mouth. "Clean them off now." Jennie did just as he asked, licking and sucking on the fingers, "That's so hot baby girl."

Dean moved back down and parted her legs before letting the tip of his tongue run over her pussy. He planted a small kiss on it and Jennie bit her lip in anticipation. He lets his tongue slide between the fold. When reached her clit he circled around it, arousing her further before flattening his tongue and rubbing it.

"Oh Dean…Yes…Oh Please!" She begged him. Just that one little movement was already sending her over the edge, "Oh…Oh…D-Dean!"

He flicked his tongue over repeatedly bringing her to a hard mind blowing orgasm. Her juices started dripping out onto the bed and he licks it all up before sticking his tongue inside her. He pulled away just before she was about to reach another orgasm and pressed his whole body against her.

Jennie felt his cock between her legs and start thrusting up with her hips in a vain attempt to get him inside of her. Instead he kissed her, their tongues meeting. She could taste herself on him and this makes her want him more.

Finally he granted her wish by driving his thick cock deep inside her, "UHHH." A loud moan escapes her mouth as he began thrusting harder into her.

"Feels so fucking good my pet." He moaned and then bit down hard on her neck. He nibbles and licks her neck over and over.

Dean continued and his pace quickened as he lifted her legs onto his shoulders, leaving her resting on my upper back. Pulling her closer, he plunged his cock deeper. Her muscles start to spasm around him in ecstasy as she reached her climax again, "Dean…Don't stop! Please…Harder."

"You want it harder?" he asked. "Want it to hurt?"

"Yes master!" she begged him. "Take me hard!"

Dean granted her request and thrusted into her harder than ever before. There was no way she would ever be able to move after this.

"Scream Jennie. Scream my name now!" he ordered.

"DEAN!" She cried out in pain and pleasure as the orgasm took over her body.

Dean smiled down at her and he knew he close too. Once she was done he removed himself from her and moved up the bed, "Suck it. Make me cum in that perfect mouth."

Jennie sat up and little and did as he asked. Soon she felt the hot salty juice in her mouth as he came, licking it all up so not to disappoint him.

When he was satisfied he climbed off the bed and got dressed, "I want this room cleaned up and you dressed again. Nothing better be out of place you hear me?"

"Yes sir." Jennie said, "Thank you sir."

Dean zipped up his jeans and smiled over at her, "As long as you give me what I want I am be a very good man. You fuck with me once and I will be your worse enemy."

"I understand." Jennie.

"Once you're done in here I want to see you out in the torture room. I have a few more things I want you to do today."

"Yes sir." She said.

Dean slipped his shirt over his head and walked out the door leaving Jennie alone to take just a small moment to recover. She knew as time went on it was going to be harder and harder to please that man.

* * *

><p>Castiel walked into the main hall and saw a few of his superiors standing around in a circle, "You wanted to see me."<p>

Zachariah turned to him with his hands behind his back and smiled, "Yes Castiel, come in please."

Castiel did as he was asked and walked up to Zachariah, "What can I do for you?"

"We have a job for you. Lilith is getting closer to breaking the final seals. You know what that means."

"Yes I know."

"Good. What we need for you to do is to get the Winchesters back together. They will find her and stop her." Zach smiled.

"But Dean Winchester is in hell. He has no desire to come back to earth." Castiel said.

"We know this and that is why you are to go there and get something that will make him come back. Her name is Jennie. Word is she is his prized possession. Get her and Dean will come after her."

"What if he doesn't?"

"Oh he will. She is the one he has chosen to carry his future children. He will do anything to keep her with him. Get her and we get him. The first thing he will do when he gets to earth is find Sam. Leave the rest to us." Zach said, "No go."

Castiel was always one to do as he was told and seconds later he was gone.

* * *

><p>Sam stood over the young woman with a knife in his hands, "Please…..I don't know anything." She begged him.<p>

"You're lying." Sam said, "Tell me where Lilith is."

"I don't know who you're talking about." She cried.

"No, but the demon inside you does." Sam said. He and Rudy had tracked down one of Lilith's servants but now she was hiding inside a school teacher. The old Sam would have let her go but not this time. He didn't care what it took. He wanted Lilith and he wanted his brother back.

"What are you talking about?" the woman cried, "Please."

Ruby stood there watching and sighed, "Just killed her. The demon isn't coming back out."

Sam glanced over at Ruby and then looked back down at the girl, "Sorry." He said before sticking the knife deep into her heart.

The woman screamed out in pain and soon they saw the demon inside her die. Sam pulled the knife out and licked the blood clean. Ruby stood back and smiled a she watched him. Things were going as planned. Sam was turning. Lilith was going to be pleased.

* * *

><p>Jennie slipped on the red nighty Dean had left for her and walked out of the room to see what else she could do to make him happy. She followed the screams down the hallways and her heart was pounding. She hated the torture room more than anything. Every time she passed the room memories came flooding back to her. She just had to tries as hard as she could to push them out of her mind.<p>

Just as she was about to walk into the room she felt someone grab her from behind and push her into the wall, "Where do you think you're going pet?" a demon named Marcus asked, "A little too far from daddy aren't you?" he said and licked the side of her face, "You taste damn good."

"Let me go." Jennie said and tried her best to push him away.

Marcus laughed and pushed her harder into the wall, "Not until I get something from you. I hear the way you scream his name at night. Lets see if I can do better." He said and moved his hand between her lets and brushed his finger tips over her cloth covered pussy, "Still so wet."

"Please…Please let me go." She begged him, "Dean will just get mad."

"Dean will never know. I won't tell him." Marcus said and nibbled on her ear as he pushed the fabric aside and moved his finger over her fold, "Can't wait to feel you wrapped around me."

"Dean!" Jennie yelled.

Marcus pulled away and slapped her hard across the face, "Shut up!" he yelled and plunged two fingers inside of her causing to her to scream out again.

Dean heard Jennie's cried for help and looked up. He dropped his blade and ran down the hallway to see what was going on. When he rounded the corner he saw Jennie against the wall and Marcus with his hand between her legs. His blood began to boil and he balled up his fist, "Hey! What the fuck is going on here?" Dean yelled.

Marcus pulled away from her and Jennie dropped to the ground. "Dean….she came onto me man. She's nothing but a slut."

Dean walked slowly over to him with anger in his eyes, "Did she now?" he asked and glared down at Jennie who was shaking her head no.

"Yeah. You should keep her on better lock down." Marcus said.

"Maybe." Dean said. He grabbed Marcus by the throat and slammed him into the wall. His eyes turned red and he squeezed harder and harder. Marcus tried to break the grip but no one was a match for Dean.

Seconds later Marcus fell to the ground….dead.

Jennie was sobbing as she looked up and saw Dean staring at her, "I didn't do…."

"Get up!" he yelled.

Jennie did what he said and Dean jerked her to him, "Did you ask him to touch you?"

"No I swear." She cried, "I would never do that to you. Please Dean."

"Did you like it?" Dean asked, "Did you like him touching you the way that I do?"

"No."

"I think you're lying." Dean said and jerked her down the hallway.

"No Dean please. Please don't do this." She begged him.

"Shut up!" Dean yelled at her.

He pulled her back down to the cages and threw her in the first one, "You are going to stay in here until I want you again…..if that ever happens." He said and slammed the door.

Jennie got up and ran to the door, "Dean! Come back please!" she yelled as she sobbed harder and harder.

She put her back to the wall and slid down. Dean was done with her and it was killing her inside. She needed him. She wanted him to want her. She would die without him.

"Jennie?"

Jennie looked up and saw a bright light in front of her and she scooted into the corner, "Who-Who are you?"

"Someone who is saving you."

Jennie saw the bright light coming to her and closed her eyes. That is the last thing she remembered. When she finally opened her eyes she found herself on a park bench still in her nighty. She knew this place. She was home.

"Oh no." she said. Dean was going to be pissed.

***Please review! Next Dean will find she's gone and the Sam and Dean reunion : )**


	4. Chapter 4

Jennie stood up and looked around her, "Oh no no no." she said. This was not good. Dean was going to flip. She was never supposed to leave him and she never wanted to either.

"You're going to be ok now."

Jennie heard that same voice she heard in the pit and turned to see the same man, "You? What did you do?" she asked him, "You have to send me back right now."

"You're safe now." Castiel said. "I saved you. You where chosen."

"Then UN choose me. You don't understand. Dean is going to be so mad at me for leaving. I dont want him to be mad at me."

"Everything I am doing is for a reason and you need to trust me."

"Who are you again?" she asked, "Right now I am so confused."

"I'm an angel of the lord. I was told to save you so I did. That is all you need to know right now. Find Sam Winchester and everything will be ok."

"Sam Winchester. Isn't that…."

"Dean's brother. He will keep you safe."

"From what?" Jennie asked and Castiel was gone, "You can't leave me here!" she yelled. She was so screwed. She was going back on the rack for sure. Maybe she could find Sam and he could help get her back home. He was her only chance.

Dean walked back down the dark hallways toward the cage where he had tossed Jennie. He was pissed at her but she was going to make it up to him in other ways. She was special to him and he had chosen her over all other to carry his children and it was time for her to give him what he wanted.

Dean opened the cage and walked inside, "Jennie." He said and looked around and there was no sign of her, "Jennie? Where the fuck are you?" he called out again and walked around the room, "No No No. He said and ran out of the room, "Jennie!" he screamed.

"What's wrong Dean?" one of his many servants asked.

"Where the fuck is Jennie?"

"We haven't seen her."

Dean gripped him by the collar and slammed him into the wall, "Don't lie to me!"

"I'm-I'm not sir."

Dean let him go and turned around. There was only one other place she could be. Dean looked up and growled. He was going to find her and bring her back if he had to rip the whole world apart to do it.

"Tell everyone to stop what they're doing. I want Jennie found at all cost. No one rest until I have her back."

"Yes sir. We stop at nothing." He said and was gone to tell everyone they were on a mission to bring back their future queen.

* * *

><p>Sam licked the blood from the wrist of the demon and smiled as she faded away, "I warned you." He smiled as he eyes closed. Soon he was going to be strong enough to kill Lilith and get Dean back. He was willing to do whatever it took.<p>

The door to the cabin flew open and Sam turned around and saw Ruby walking in, "Where the hell have you been? I've been calling for hours." Sam said.

"I had to check on something and I'm glad I did. We need to go find someone." Ruby said.

"Who?"

"Her name is Jennie and trust when I say you want her."

"Why would I want her?"

"Trust me Sam. Let's just say she can help get Dean back." Ruby smiled. She knew just who Jennie was.

Hearing that this girl could help him get Dean was all Sam needed to hear. He put the knife in his jeans and jerked his bag off the table, "Let's go." He said and hurried out the door. Nothing was going to stop him for getting Dean out of hell.

Jennie walked around the small town trying to find somewhere that she could rest and maybe take a shower. She came upon a small motel and even though she had no money she hoped they would see her and show her mercy.

She walked into the office and walked over to the old lady working the deck, "Hi." She said and wrapped her arms around her body trying to hold her ripped clothes together.

The old lady looked up and gasp, "Oh child what happened to you?"

"Long story."

"Where you attacked? Are you hurt?"

"Not yet." Jennie said, "I don't have any money but I was hoping I could just have use one of your rooms to clean up a bit. I'll leave right after that I promise."

The lady looked Jennie over and her heart broke for this young girl. She could see the fear and pain in her eye, "You stay as long as you like." She said and handed Jennie a key, "My granddaughter is about you size. I'll go find some clothes and bring them to your room. Should I call the cops or something for you?"

"No! I mean no. No cops. I'm fine. Just a little too far away from home but it will be ok. I just need a little rest."

"Ok dear. You head on to your room and I'll leave the clothes out by the door."

"Thank you so much."

Jennie walked out of the room and the old lady smiled as he eyes went black. She looked down at the dead body of the owner on the floor and drained his blood into a class, "Sir I found her. She is at the red fire motel." The lady said. Dean was going to be please.

Sam and Ruby pulled up to the motel and parked the car. Sam was going to be in for a shock when Dean got here. Everything was falling into place and Lilith was going to be happy.

"Are you sure this is the place?" Sam asked as he turned off the impala.

"I'm sure. I know she's in there." Ruby said, "Room 15."

"Ok let's go." Sam said and jumped out of the car.

Jennie stepped out of the shower and wrapped the towel around her bruised body. She wiped the steam off the mirror and lightly touched her red face. Dean always did like to leave a mark. Jennie was afraid this was going to be the only thing she had to remember him by.

She walked out of the bathroom and looked around the room. It was quiet. No screams and worse was no Dean waiting on her, waiting for her to give him what he wanted.

Jennie walked over to her door and opened it up and saw a pair of short and a shirt by the door and she smiled. Just as she leaned over to pick them up someone grabbed her and pushed him back into the room and slammed the door, "Please don't hurt me." Jennie begged as she looked up at the tall man that was holding the gun to her head.

"Are you Jennie?" he asked.

"Y-yes." She said.

Sam lowered the gun and put it back into his pocket and looked over at Ruby, "Is this her?"

"Yes it's her."

"Who are you? Did he send you?" Jennie asked, "Is he mad at me?"

"Calm down. Who are you talking about?" Sam asked. Thunder and lightening began to strike outside. The motel began to shake and they three of the froze, "What the hell is going on?" Sam asked.

"Oh no." Jennie said and backed away from Sam.

"This is about to get ugly." Ruby said.

"Ok somebody better fucking talk!" Sam yelled.

"He's coming." Jennie said, "He's mad. It's all my fault."

"Who is coming?" Sam asked.

"D-Dean." Jennie said and just then the motel door flew open and Sam pointed the gun out the door and waited.

Seconds later Dean walked up to the door with a smile on his face, "Hey Sammy. Long time no see."

Sam was frozen to the floor. After all these months there was Dean and he looked like nothing was wrong. He looked….happy. "Dean." Sam whispered.

"We need to talk." Dean said and walked into the room and Jennie back up against the wall. She had no idea what was about to happen to her or any of them. Dean never smiled unless someone was going to die.

***PLEASE REVIEW! PLEASE!**


	5. Chapter 5

Jennie stood frozen against the wall as Dean entered the room. Her heart was pounding in her chest. She knew she was in trouble and it would be the rack for her. There was no way out of it. Even though it was not her fault she felt like it was and she must be punished.

Dean glared over at her for a moment before turning his attention back to Sam, "Sammy. You look well." He said and crossed his arms, looking between Sam and Ruby. "I see a few things have changed for you as well." He could tell what was going on with his brother.

Sam was still in shock to be standing there in front of his brother. The brother that had died and went to hell. The brother he had been trying to save, "Dean. I can't believe it." Sam said. "How are you?" Sam asked and it felt like a stupid question but that was all he could come up with.

"Better than ever." Dean said with a smile on his face, "A little different you might say but I love where I am." Dean looked from Sam and over at a frightened Jennie, "We can catch up as soon as I take care of a few things." Dean walked over to her and folded his arms over his chest. "Jennie, Jennie, Jennie. I think you have some explaining to do.

"You know her?" Sam asked

"I should. She's mine" Dean replied as he kept his eyes glued to the young girl, "I think we need to go have a little chat. I am not happy with you right now."

"Y-yes sir." She swallowed hard. Part of her was just ready to get this over with. She moved away from the wall and walk closer to him.

Dean wrapped his arm over her shoulder and turned back Sam, "I have to say, I expected a better place than this." He looked around the old cabin, "Yeah this won't work. I'll find us a better place and give you a call." Dean told Sam before vanishing with Jennie.

Sam blinked as Dean disappeared. He could believe it. Did he really just see that? He brother, the hunter, strolls in here as a demon and act like nothing was wrong? Sam turned to Ruby and frowned, "What the hell was that?"

"Looks like Dean has joined the winning team. About damn time too." She said.

"Did you know about this?"

"I may have heard rumors but I have been up here with you most of the time."

Sam sighed, "Well at least he will take the news about us a little better."

"See…this just keeps getting better and better." Ruby smiled, "We still have work to do so let's get to it" She said as she pulled out her knife and Sam smiled.

* * *

><p>Dean took Jennie to a penthouse in the city and as soon as they got there he made himself a drink. He had been very quiet and that made Jennie even more nervous. This wasn't like this at all. "Dean…"<p>

Dean held up his hand hushing her and Jennie stopped. Dean took the glass in his hand and turned to face her, "I'll let you know when you can talk." He took a drink and walked over to her, "You know I am not happy with you at all right now. Can you imagine how I felt then I woke to find that you were just gone? I searched everywhere. What I can't figure out is how you got out of the room to begin with. Who have you been talking to Jennifer?"

"No one I swear. I don't know what happened. I really don't. I didn't want to leave you. I promise, Dean." She said.

Dean eyes her as he takes a drink, "Why don't I believe you? People just don't up and vanish out of hell. Trust me I know. So what are you hiding? Who pulled you out?

"I didn't talk to anyone or do anything. I wanted to come back to you. I promise." She teared up, "It was one man…an angel or something but I never asked for him to come. Not once. I wanted to stay with you, Dean."

Dean stared deep into her eyes, "You better not be lying to me. If I find out that you are you know what will happen."

Jennie nodded, "I know. I promise will make this up to you. I'll do anything to prove that with you is where I want to be."

Dean smiles a little, "Just what I like to hear, pet. But you know either way I would be keeping you." He moved in closer to her, "If you ever leave again I will personally kill you slowly, every day for eternity" He said and that look in his eyes told Jennie that he was dead serious.

Jennie nodded and bit on her lower lip, "You know when you bite that bottom lip of yours, it makes you look like an innocent little girl." Dean pulled her against him again making her shiver .Her hands were on his shoulders and he held her against him, his face mere inches from hers she could feel his breath on her lips, "An innocent little girl I want to corrupt." His lips crashed on hers making her moan. He held her hips tightly digging his fingers into her soft skin causing small bruises to form. She whimpered at the pain.

Dean's hand left her hip and moved under her skirt to her thong. His finger slid along the string to the front of her thong and ran his index finger up and down the cloth teasing her nub. She let out a small moan into his mouth. "I'm going to show you who you belong to," he said lifting her legs and wrapping them around his waist. Her hands ran up his arms and to his biceps where they were bulging out the sleeves of his black t-shirt. "You want me to please you baby?"

She nodded and grinded up against him making him moan, "Yes, please Dean."

"Yeah that's it beg for me. Beg for your master."

"Dean please…" She said again, knowing thats what he wanted.

His lips captured hers again into a hot lustful kiss. Her hands were on the back of his head pulling him closer to her just like he wanted.

**To be continued…..**


End file.
